N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide → 1H-Pyrrolo(2,3-c)pyridin-5-amine

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Reaction Steps

5-Acetylamino-1H-pyrrolo[2,3-c]pyridine (0.61 g, 3.5 mmol) was heated at reflux in methanolic KOH (2M, 15 mL) under nitrogen for 8 hours. The solvent was evaporated in vacuo and the residue partitioned between dichloromethane (100 mL) and water (100 mL). The two layers were separated and the aqueous phase was extracted with n-butanol (3×100 mL). The combined organics were evaporated in vacuo and the residue chromatographed on silica eluting with 5 to 10% MeOH in DCM followed by a gradient of 90:10:1 to 80:20:1, DCM:MeOH:NH3 to give the title compound (0.384 g, 83%) as a red solid. mp 183°-186° C. 1H NMR (360 MHz, d6 -DMSO) δ 4.95 (2H, br s), 6.13-6.15 (1H, m), 6.52 (1H, s), 7.34-7.37 (1H, m), 8.17 (1H, s) and 10.90 (1H, br s).

Provenance & Evidence